A unique offsite experience in Chicago

A colourful city of endless opportunity

Chicago is the country's third most populous city, much to the dismay of the visionaries who dreamt Chicago would one day surpass New York City in its grandeur.

Nevertheless, Chicago has developed a unique character with its beautiful parks, impressive high-rise structures and iconic art and entertainment scene. These attributes have made the city a popular tourist attraction and an exciting location for a corporate offsite retreat.

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Why 

Chicago

?

Why choose 

Chicago

for a retreat?

There are few cities in the world with more cultural diversity than Chicago. A drive through the city is like a trip around the world as you pass myriad cafés, restaurants, clothing outlets and grocery stores.

This mixed culture is reflected too in the variety of team-building activities on offer. In a single day, your team can learn stand-up paddleboarding, hop on a boat cruise, play volleyball on the beach and sing their hearts out at a karaoke bar!

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Team building activities in

Chicago

We've put together a list of

team-building activities for company retreats in

Chicago

, including options that work well for both small and large teams.

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Yoga in Chicago
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Karaoke in Chicago
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Kayaking in Chicago
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Food Tour in Chicago
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Laser Tag in Chicago
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Go Karting in Chicago
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Volleyball in Chicago
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Boat Cruise in Chicago

Sample

Chicago

Retreat Itinerary

Along the Chicago Riverwalk, Millennium Park, and vibrant areas like West Loop, this Chicago retreat agenda combines structured sessions with an architecture or food-focused experience and relaxed evenings in the city.

Day 1: Arrival & Downtown Introduction

City arrival, skyline views & easy start

  • 13:00–17:00Airport transfers & hotel check-in (Downtown / River North)
  • 18:00–19:30Walk along the Chicago Riverwalk & Millennium Park
  • 20:00–22:30Group dinner in a classic Chicago restaurant
  • 22:30+Optional drinks in a rooftop bar

Day 2: Work & Chicago Experience

Focused sessions with a local highlight

  • 08:30–09:30Breakfast at hotel
  • 09:30–11:00Plenary session (team alignment & goals)
  • 11:00–11:30Coffee break
  • 11:30–13:00Breakout workshops
  • 13:00–14:30Lunch near the hotel
  • 14:30–16:00Workshops or brainstorming
  • 16:00–19:00Main activity: Architecture river cruise or deep-dish pizza tour
  • 20:00–22:30Dinner in West Loop

Day 3: Exploration & Final Evening

Flexible time & iconic city moments

  • 08:30–09:30Breakfast at hotel
  • 10:00–11:00Wrap-up session & key takeaways
  • 11:30–15:00Free time (Art Institute, shopping, or lakefront)
  • 15:00–18:00Relaxation or optional visit to Willis Tower Skydeck
  • 21:00–lateFarewell dinner with skyline views

Day 4: Departure

Easy wrap-up

  • 08:30–10:30Breakfast & informal chats
  • FlexibleAirport transfers & departures

United States retreat experiences

FAQs about company retreats in

Chicago

Is Chicago a good destination for a corporate offsite?

Chicago is a strong option for teams that want a big-city experience with architecture, food, and lakefront views. It combines business-friendly infrastructure with a lively social scene, making it easy to balance work sessions with memorable group experiences.

How easy is it to travel to Chicago for a team retreat?

Chicago is highly accessible via two major airports, O’Hare International Airport (ORD) and Midway International Airport (MDW). O’Hare is about 30–45 minutes from downtown via the CTA Blue Line or taxi, making arrivals relatively straightforward for large groups.

What is the best time of year to plan a corporate retreat in Chicago?

Late spring and early autumn tend to offer the best conditions, with temperatures typically ranging from 60–75°F. Summers are lively but can be humid, while winters are cold and better suited for indoor-focused retreats.

Which areas are best to stay in Chicago for a company retreat?

The Loop is ideal for business-focused stays and easy logistics, River North offers great dining and nightlife, West Loop has a more modern and food-driven atmosphere, and Lincoln Park provides a quieter, more residential feel.

What makes Chicago different from other corporate offsite destinations?

Chicago stands out for its mix of architecture, culture, and accessibility. The city feels more structured and navigable than many large US destinations, which helps teams plan a company retreat in Chicago without complex logistics.

What team-building activities can you organize in Chicago?

Groups often choose architecture boat tours on the Chicago River, improv workshops at Second City, food tours in West Loop, lakefront bike rides, or sports events depending on the season.

How long should a company retreat in Chicago last?

A typical Chicago retreat runs for about three to four days, which allows teams to include structured sessions, one or two standout activities, and group dinners without overloading the agenda.

Is Chicago an expensive destination for corporate retreats?

Chicago sits in the mid-to-high range for US cities. While not as costly as New York or San Francisco, accommodation and dining can still add up, though there are enough options to adapt to different budgets.

What are the best day trips for a team retreat in Chicago?

Within 1 to 2 hours, teams can head to Lake Geneva in Wisconsin for a more relaxed lakeside setting, or explore nearby nature areas like Starved Rock State Park for hiking and outdoor activities.

What kind of food and dining experiences can teams expect in Chicago?

Chicago’s food scene is a major highlight, from deep-dish pizza and steakhouses to Michelin-starred restaurants. Group dinners, food tours, and private dining experiences are easy to organize across the city.

💛 Wall of love 💛

We recently worked with Surf Office to plan an offsite for our team in Sintra, Portugal and the experience was excellent. Elke went above and beyond throughout the entire process, even driving to visit the location herself to ensure everything was perfect. She was instrumental in securing a restaurant that opened exclusively for our group, making the experience truly special. The hotel was lovely, with breathtaking views that provided the ideal backdrop for both work and relaxation. The space was perfect for connecting, brainstorming, and fostering team collaboration. Every detail was thoughtfully managed. We would wholeheartedly recommend Surf Office to others looking to host memorable and productive retreats!

Natasha
Chief Human Resources Officer

Romane LeBrec-Foulatier was a fantastic partner in planning this event. She did a wonderful job of introducing the planning project via Coda and then was extremely helpful and conscientious in helping us plan toward the event. I always felt that I could depend on her follow-up and she was clear and articulate in her guidance. She was also proactive in flagging items that needed extra consideration or in raising potential issues with the schedule or venue or planning. We really loved the Coda site that she created to for planning and also the Coda dashboard that we shared with the team; the team found it very helpful as well. Lastly, Romane was critical in helping on our last day in France when the taxi drivers were on strike - she very quickly implemented a contingency plan and helped us communicate it to the team through the Coda site. Similarly. Álvaro Pérez-Segnini was very helpful in helping us choose the Chantilly location. He understood the parameters of the offsite and got back to us with multiple proposals in a limited time frame. He helped us understand which option would be the best for us and he helped us negotiate the best space and the best price.

Jen
Operations and Administration

Great offer - hotel did fit perfectly with our expectations. Danielle who took care about our company did a great job, was super available before the event and was a great help to accommodate with every impediment and change we faced and find the best solution for us. Also during the event, she was always available to make our stay a awesome moment.

Jean
Senior Director of Engineering

We had such a fantastic experience working with SurfOffice! It was our very first time getting external support for our company retreat – and we couldn’t have asked for a better partner. From the very beginning, we felt incredibly well taken care of. The regular check-ins helped us go through every detail and made sure nothing was overlooked. And in the end, everything turned out exactly as we had hoped! The implementation was seamless, and the SurfOffice team was always there to support us – even during the retreat itself. A huge thank you for your time, effort, and amazing support. You truly made our retreat an unforgettable experience. We can’t wait to work with you again next year!

Victoria
Operations & Office Manager

We had an amazing experience! Everything was perfectly organized from A to Z. As a vegan company, it’s usually quite difficult to find places that can fully accommodate our needs — but the Surf Office team handled everything with ease. They weren’t afraid of any request, preference, or extra thing we asked for. The communication was smooth, fast, and friendly throughout the entire process. We truly appreciated the attention to detail and how flexible and supportive the team was. We can’t recommend them enough!

Elya
Executive Assistant

I have just wrapped up my fourth annual retreat with Surf Office, this time hosted in Mallorca, and as always they created the perfect experience for myself and my team. Our sales representative Giselle was brilliant, she listened to what we needed and came back with venue options that were perfect for our budget and vibe. Romane was my main contact throughout for the logistics. We had some last-minute changes and she managed everything like a pro, even securing us refunds when we had a cancellation. This is why I keep coming back to Surf Office for our annual event. They actually care about making the retreat something special. It's that personal touch that makes all the difference.

Claire
Head of Operations and Community

We recently worked with Surf Office to plan an off-site retreat for 105 people, and the experience from start to finish was absolutely seamless. From the initial proposal stage, through planning, to on site support, everything went perfectly, and we honestly couldn’t have done it without them. A special thanks to Alvaro and Elke. Alvaro was our initial intro to Surf Office, and working with him on proposals for the retreat was a pleasure. He understood our needs and helped shape the retreat options. Once the planning stage began, Elke took over as our retreat planner. She made everything feel completely in hand and ensured that every detail was looked after. Nothing was ever too much to ask. On site, Fernanda and Bibi were fantastic. With their support, everything ran super smoothly, and we had all the help we could possibly need. The feedback we received was overwhelmingly positive, everyone LOVED the trip! A huge well done to the whole team. We couldn’t recommend them enough.

Kevin
CEO

Our team had an amazing experience working with Surf Office. From the very first conversation, their team was incredibly communicative, organized, and attentive to every detail. They made the entire retreat-planning process smooth and stress-free from venue coordination to activities and logistics, everything was handled with care and professionalism. What really stood out was their responsiveness and ability to anticipate our needs before we even mentioned them. It’s clear they truly understand what makes a company retreat successful. If you’re looking for a partner who combines efficiency, great communication, and genuine hospitality, look no further than Surf Office. We couldn’t recommend them more!

Ierusha
Sr Executive Assistant

I had a wonderful experience working with the SurOffice team. I’d like to specifically highlight Raquel and Giselle, who have been incredibly supportive from day one. They were always proactive in checking in, handling last-minute requests, and doing so with the utmost professionalism and politeness. This was my second time working with the team, and it was an absolute pleasure. I would definitely look forward to collaborating with them again in the future.

Sandhya
HR Operations Manager

Team building activities

The most popular team building activities are surf lessons, SUP lessons and tapas night but there are plenty more to choose from.

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